Cross-dressing in acting is as old as acting itself. Though at first it was because women weren’t allowed on stages, you can see why the kinkiest of traditions would endure: It can be funny, dramatic, and, if the person is blessed with good genes to begin with, kinda hot!
Tonight, Puerto Rican actor Amaury Nolasco becomes the latest Latino to cross-dress onscreen when his new comedy, Work It, premieres at 8:30 p.m., (EST) on ABC. Which other Latinos have traded their moustaches for lipstick or bound their breasts onscreen? Check out our list of favorite gender-bending performances!
Amaury Nolasco (Work It)
When his fellow salesman buddy pulls on pantyhose and fake boobs to get a job at a pharmaceutical company, Nolasco’s character, the womanizing Angel, gets into the act with surprising hip-swaying relish only made funnier by the fact that he has a jaw like Paul Bunyan.
Salma Hayek (Frida)
Before she played a bearded circus lady in Cirque Du Freak: The Vampire's Assistant, Hayek pulled back her hair and put on a suit in Frida, in a scene in which the artist, who often painted herself wearing menswear (and that ‘stache!), posed for a picture with her family. Her onscreen dad’s reaction: “I always wanted a son!”
John Leguizamo (To Wong Foo, Thanks for Everything, Julie Newmar) is hilarious and very, very convincing as drag queen Chi-Chi, who can rock heels, satin mermaid dresses and Carmen Miranda hats and provides a lot of the film’s big laughs.
Gael Garcia Bernal (Bad Education)
Cross-dressing is usually played for laughs onscreen, but not in this Pedro Almodovar melodrama, in which Bernal plays three characters. One of them is Zahara, a nightclub singer who blackmails a priest that abused him as a Catholic-school student, all while looking like a walking, talking Mac ad, with green eyes are set off by eyeliner and pouty lips accentuated by red lipstick.
Antonia San Juan, All About My Mother
Transsexual actress San Juan was one of the most delightful parts of Almodovar’s instant classic film, in which a mother goes to Barcelona in search of her dead son’s transsexual father. San Juan plays the mother’s best friend, who has a very funny, show-stopping monologue onstage at a theater, in which she talks about authenticity by listing all the work she’s had done on her body.
Miguel A. Nuñez, Jr. (Juwanna Mann)
Despite his height, Nuñez’s surprisingly soft features make him a perfect candidate for passing as a woman, which he does in this comedy about a baller who gets kicked out of the NBA and poses as a woman to play in a women’s league.
Cameron Diaz (Charlie’s Angels)
Who would have thought that girly-girl Diaz could be transformed so convincingly into a dude? When she and Drew Barrymore don the pants and the facial hair during an undercover operation in contrast to the sexy women’s wear they have on during the rest of the movie, we’re sure more than a few theatergoers must have felt a little funny inside.
Renoly Santiago (Con Air)
Teeny tiny Santiago looks hilariously out of place among big, beefy convicts packed into a prisoner transport plane that they then take over. As Ramon “Sally-Can’t-Dance” Martinez, he preens and sashays in a purple dress, while the other jailbirds look on and accept his role, with one con even slipping a gun magazine down Ramon’s dress.
Wilson Jermaine Heredia (Rent)
Can you do a backflip in platform high-heeled boots? In Rent, as gay transvistive infected with AIDS, Heredia out-chicks the chicks and manages to pull our heartstrings with his singing and his tragic story.